Compositions of matter for producing a softening effect on textiles



Patented Nov. 27, 1951 COMPOSITIONS F MATTER FOR PRODUC- ING A SOFTENIN G EFFECT ON TEXTILES Otto Albrecht, Neuewelt, Switzerland, assignor to Ciba Limited, Basel, Switzerland, a Swiss firm No Drawing. Application June 19, 1947, Serial No. 755,709. In Switzerland June 28, 1946 4 Claims. (Cl. 252-8.75)

According to this invention, fibrous materials and are softened in an advantageous manner by treat- 0 ing the material with an aqueous dispersion 01 a partial ester of a higher fatty acid and a glycol, 2 which dispersion contains as a dispersing agent 5 H: a water-soluble salt of a condensation product of an N-methylolamide of a higher fatty acid I with a mercapto-carboxylic acid and, if desired, N H a lime-resistant sulfonation product of a, benzimidazole having attached to the a carbon atom a side-chain of at least 12 carbon atoms. wherein As partial esters of fatty acids of high molecular weight which are used in the invention in dispersed form, there may be mentioned esters R of ethylene glycol, diethylene glycol, triethylene 15 glycol or even higher polyglycols with fatty acids is the acyl radical of the fatty acid employed in of high molecular weight, especially fatty acids the condensation. Products of these const tutions containing at least 12 carbon atoms. Polyare described in U. S. Patent No. 2,337,220.

glycols as mentioned above correspond to the These examples demonstrate that an acylated formula amino group corresponds to the formula HO (CH2-CH2O) r-CHz-CHPOH %0 wherein a: is at least one.

As condensation products of N-methylolamides of higher fatty acids with mercapto-carboxylic l acids, there may be used, for example, condensation products of the formula wherein z CHr-S R c is an acyl radical of a carboxylic acid and R1 is w e 1 is a amino D acylated With a f y hydrogen or a hydrocarbon radical, for instance, acid with at least 16 carbon atoms and R is an alkyl radical which may be substituted; R1 alkylene. Examples of condensation products of may be, for inst nce, methyl, ethyl or a methyl this kind are, for instance, the condensation prodradical substituted by an acylated amino group. ucts obtainable from thioglycollic ac d As an example of this kind of substituted methyl palmitic acid N-methylolamide. stearic acid,iN- r dic l th following may be cited; methylolamide or oleic acid-N-methylolam dc, which contain the atomic grouping CH2"'NH CO R 0 wherein --COR has the meaning given above. As lime-resistant sulfonation products of a benzimidazole having attached to the 1!. carbon atom a side-chain of at least 12 carbon atoms,

the dispersions used in the invention may conin which tain, for example, the following products: Sulfonic acids of benzimidazoles having attached to the -carbon atom a side chain of at least 12 carbon atoms, which benzimidazoles may, if desired, be aralkylated, for example, the sodium is the acyl residue of the fatty acid used. Ex- Salt of 1-,L-heptadecyl-benzimida l 1- amples of condensation products with the aforeulfoni acid.

mentioned atomic grouping are compounds o In order to prepare the dispersions to be used the formulae in the invention, the partial esters of higher fatty 0 acids and a glycol may be introduced, advantageously in the molten state in the case of comy pounds which are solid at room temperature, into concentrated solutions or pastes of the above or{ mentioned dispersing agents while rapidly stiract aces ring, advantageously at a temperature above the melting point of the substance to be dispersed.

The dispersions of the present invention may be described as compositions of matter producing a softening eiiect on textiles which compositions of matter comprise an aqueous dispersion of a partial ester of a higher fatty acid and a glycol, said dispersion containing a water-soluble salt of a condensation product of an N-methylolamide of a higher fatty acid with a mercapto-carboxylic acid.

The softening process of the invention may be carried out by impregnating the material at room temperature or a moderately raised temperature with an aqueous liquor containing a small quantity of a dispersion of the kind described above, for example, i to grams per liter, and then Squeezing or centrifuging the material and drying it.

Among the fibrous materials which can be softened by the process of the invention there may be mentioned: Animal fibers such as wool or si cellulosic materials such as cotton, linen, cellulose, paper, and also regenerated cellulose including staple fibers of regenerated cellulose: cel-= lulose acetate artificial silk; synthetic materials produced, for example, by polymerisation or condensation, for example, polyamide fibers; and also leather.

The following examples illustrate the invention. the parts being by weight unless otherwise stated, and the relationship of parts by weight to parts by volume being the same as that of the kilogram to the liter:

Example 1 Chlorinated wool is softened in the following manner:

A bath is prepared which contains, per liter, 1 gram of a mixture of 25 parts of diethylene glycol monostearate. 14 parts of the sodium salt of a. carboxylic acid obtainable by the condensation of stearic acid-N-methylolamide with thioglycollic acid and also 11 parts of the disodium salt of N benzvl- -hepta decyl-benzimid azole disul onic acid. The wool is worked in the bath at a liquor ratio of 1:10 for /4 hour at room temperature and centrifuged and dried. The wool so obtained is distinctly softer than the untreated material.

The dispersion used above is prepared in the following manner:

T68 parts of the sodium salt of the carboxylic acid obtainable by condensing stearic acid-N- methylolamide with thioglycollic acid, and '72 parts of the disodium salt of N-benzyl- -heotadecyl-benzimidazole disulfonic acid are added in portions while stirring to 100 parts by volume of water at 95 C. Then a further 60 parts of the disodium salt of N-benzylr-heotadecvl-benzimidazole disulfonic acid are introduced while stirring, advantageously with the introduction of steam heated to 100 C. In the course of about 30 minutes 300 parts of diethylene-glycol monostearate heated at 90 C. will have been stirred into the homogeneous paste so obtained. The stirring is continued for a short time, then the temperature is allowed to drop to 60 C., and its weight is made u to 1200 parts, and the whole is then allowed to cool while stirring. In order to prepare the treatment bath the concentrated dispersion is boiled with times its weight of water and then further diluted.

The condensation product of stearic acid-N- methylolamide and thioglycollic acid as used above corresponds to the formula ZCHzS-CHz-C and is obtained by condensing one molecular proportion of the methylolamide of commercial stearic acid with A9, molecular proportion of thioglycolllc acid.

A similar efiect can be obtained by using, instead of diethylene glycol monostearate, the cor responding oleic acid ester and in other respects working exactly in the manner described above.

Example 21 Wool is softened in the following manner: A bath is prepared which contains, per liter, 1.25 grams of a stearic acid polyglycol ester obtained by condensing 1 molecular proportion of com mercial stearic acid with 3.8 molecular propor-= tions of ethylene oxide, and also 0.875 gram of the sodium salt of the carboxylic acid obtainable by the condensation of stearic acid-N-methylol=- amide with thioglycollic acid and 0.375 gram of the disodium salt of N-benzyl-;l-heptadecyl-ben-= rimidazole disulfonic acid. The wool is worked in the bath at a liquor ratio of 1:10 for /4 hour at room temperature and centrifuged and dried. The wool so obtained is distinctly softer than the untreated material.

The stearic acid polyglycol ester used above can be obtained by forcing 247.5 parts of ethylene oxide under a, pressure of 6 to 10 atmospheres at l50-l55 C. into 400 parts of commercial stearic acid and 15.1 parts of finely ground sodium acetate.

The dispersion used above may be prepared as follows: 525 parts of the sodium salt of the carboxylic acid obtainable by the condensation of stearlc acid N-methylolamide with thio-glycollic acid and 225 parts of the disodium salt of N- benzyl ,u heptadecyl benzimidazole disulfonic acid are heated at the boil with 3'75 parts of water, while stirring. In this manner a homogeneous paste is obtained. 750 parts of the above described stearic acid polyglycol ester heated to C. are then introduced in small portions in the course of 30 minutes while rapidly stirring. The resulting homogeneous paste is stirred cold and made up to a weight of 3000 parts by the addition of water.

A similar effect can be obtained by using, instead of the above mentioned stearic acid polyglycol ester, the oleic acid polyglycol ester ob= tainable from 1 molecular proportion of oleic acid and 6 molecular proportions of ethylene oxide.

What I claim is:

' 1. Composition of matter producing a softening efiect on textiles and consisting of an aqueous dispersion of a. partial ester of a fatty acid with at least 12 carbon atoms and a'member selected from the group consisting of a glycol and a glycol ether of the formula wherein R'CO- is the acyl radical of a fatty acid with at least 16 carbon atoms, said dispersion containing also a water-soluble salt of a sulfonated benzimidazole in which the a carbon atomof the imidazole ring is bound to an alkyl radical of at least 12 carbon atoms, the relative proportions of the ingredients being about 50 parts by weight of the ester to 28-35 parts by weight of the water-soluble salt of the carboxylic acid and 15-22 parts by weight of the water-soluble salt of the sulfonated benzimidazole.

2. Composition of matter producing a softening efiect on textiles and consisting of an aqueous dispersion of a partial ester of a fatty acid with at least 12 carbonatoms and a glycol, said dispersion containing a water-soluble salt of a carboxylic acid of the formula wherein R'CO is the acyl radical of a fatty acid with at least 16 carbon atoms, said dispersion containing'also a water-soluble salt of a sulfonated benzimidazole in which the ,u-carbon atom of the imidazole ring is bound to an alkyl radical of at least 12 carbon atoms, the relative proportions of the ingredients being about 50 parts by weight of the ester to 28-35 parts by weight of the water-soluble salt of the carboxylic acid and 15-22 parts by weight of the water-soluble salt oikthe sulfonated benzimidazole; 1

3. Composition of matter producing a softening effect on textiles and consisting of an aqueous dispersion of a partial ester of a fatty acid with at least 12 carbon atoms and a glycol ether of the formula wherein m is at least one, said dispersion containing a water-soluble salt of a carboxylic acid of the formula wherein R'-CO- is the acyl radical of a fatty acid with at least 16 carbon atoms, said dispersion containing also a water-soluble salt of a sulfonated benzimidazole in which the -carbon atom of the imidazole ring is bound to an alkyl radical of at least 12 carbon atoms, the relative proportions of the ingredients being about 60 parts by weight of the ester to 28-35 parts by weight of the water-soluble salt of the-carboxylic acid and 15-22 parts by weight of the watersoluble salt of the sulfonated benzimidazole.

4. Composition of matter producing a softening effect on textiles and consistin of an aqueous dispersion of an ester of the formula wherein R-CO- is the acyl radical of commercial stearic acid, said dispersion containing a water-soluble salt of the carboxylic acid of the formula wherein R'C0- is the acyl radical of commercial stearic acid, this carboxylic acid being obtained by condensing 1 molecular proportion of the methylol amide of commercial stearic acid with molecular proportion of thioglycollic acid, said dispersion containing also a water-soluble salt of a disulfonic acid of the benzimidazole of the formula wherein R is the alkyl radical contained in commercial stearic acid of the formula the relative proportions of the ingredients being about 50 parts by weight of the ester to 28-35 parts by weight of the water-soluble salt of the carboxylic acid and 15-22 parts by weight of the water-soluble salt of the sulfonated benzimidazole.

O'I'I'O ALBRECHT.

REFERENCES CITED The following references are of record in the file of this patent:

Chem. Glycols, pub. by Glyco Product 00., copyright 1948, p. 12. I 

1. COMPOSITION OF MATTER PRODUCING A SOFTENING EFFECT ON TEXTILES AND CONSISTING OF AN AQUEOUS DISPERSION OF A PARTIAL ESTER OF A FATTY ACID WITH AT LEAST 12 CARBON ATOMS AND A MEMBER SELECTED FROM THE GROUP CONSISTING OF A GLYCOL AND A GLYCOL ETHER OF THE FORMULA 